5-(3,3,3-Trifluoro-2-hydroxy-1-propyl)thio-3-isopropyl-7-[4-(2-pyridyl)benzyl]amino-1H-pyrazolo[4,3-d]pyrimidine

ID: ALA4476377

PubChem CID: 155538371

Max Phase: Preclinical

Molecular Formula: C23H23F3N6OS

Molecular Weight: 488.54

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CC(C)c1n[nH]c2c(NCc3ccc(-c4ccccn4)cc3)nc(SCC(O)C(F)(F)F)nc12

Standard InChI:  InChI=1S/C23H23F3N6OS/c1-13(2)18-19-20(32-31-18)21(30-22(29-19)34-12-17(33)23(24,25)26)28-11-14-6-8-15(9-7-14)16-5-3-4-10-27-16/h3-10,13,17,33H,11-12H2,1-2H3,(H,31,32)(H,28,29,30)

Standard InChI Key:  AKKCYZKIAPTKHT-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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    3.4128  -21.8371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2361  -21.8382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6470  -21.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2356  -20.4141    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4092  -20.4169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0020  -21.1287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4682  -21.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8800  -21.8409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7043  -21.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1178  -21.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7010  -20.4094    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8781  -20.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9429  -21.1256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3563  -21.8397    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.1814  -21.8388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5902  -22.5531    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4145  -22.5525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8271  -21.8370    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.5864  -21.1246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4049  -21.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6566  -20.3445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9936  -19.8644    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3323  -20.3466    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.4410  -20.0883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0550  -20.6395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6113  -19.2811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8275  -23.2669    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.4154  -23.9816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8283  -24.6959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4162  -25.4107    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.6534  -24.6954    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0664  -25.4098    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.0656  -23.9806    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.4763  -24.6943    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
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  6  1  1  0
  7  8  2  0
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  9 10  2  0
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  3  7  1  0
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 20 21  1  0
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 23 19  1  0
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 24 25  1  0
 24 26  1  0
 17 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 31 33  1  0
 31 34  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476377

   ---

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 488.54

Molecular Weight (Monoisotopic): 488.1606

AlogP: 5.17

#Rotatable Bonds: 8

Polar Surface Area: 99.61

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: 1

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 10.43

CX Basic pKa: 4.42

CX LogP: 5.11

CX LogD: 5.11

Aromatic Rings: 4

Heavy Atoms: 34

QED Weighted: 0.23

Np Likeness Score: -1.23

References

1. Jorda R, Havlíček L, Šturc A, Tušková D, Daumová L, Alam M, Škerlová J, Nekardová M, Peřina M, Pospíšil T, Široká J, Urbánek L, Pachl P, Řezáčová P, Strnad M, Klener P, Kryštof V..  (2019)  3,5,7-Substituted Pyrazolo[4,3- d]pyrimidine Inhibitors of Cyclin-Dependent Kinases and Their Evaluation in Lymphoma Models.,  62  (9): [PMID:30943029] [10.1021/acs.jmedchem.9b00189]

Source

Source(1):

• Scientific Literature